Antibacterial agents and cosmetics and clothing containing the same

ABSTRACT

Safe antibacterial agents containing macrocyclic lactones and/or macrocyclic ketones usable for suppressing the growth of indigenous dermal bacteria. Cosmetics containing these antibacterial agents can, in particular, suppress the evolution of the body odor and are efficacious in preventing and treating pimples. When introduced into clothing, these antibacterial agents achieve an antibacterial/deodorizing effect.

This application is a 371 of PCT/JP97/01710 filed May 21, 1997.

TECHNICAL FIELD OF THE INVENTION

The present invention relates to antibacterial agents used forsuppressing the growth of indigenous dermal bacteria present in derma ofthe human body, etc., and specifically safe antibacterial agentsefficacious in suppressing the evolution of the body odor and inpreventing pimples, and fragrant cosmetics and clothing containing orimpregnating carrying such antibacterial agents.

BACKGROUND ART OF THE INVENTION

Body odor of the human body, etc. is evolved by indigenous dermalbacteria that decompose secreta from sweat glands or sebaceous glands.Generally, as indigenous dermal bacteria, bacteria of the genusMicrococcus and the genus Staphylococcus which are Gram-positive cocci,and bacteria of the genus Corynebacterium, the genus Propionibacteriumand the genus Brevibacterium which are Gram-positive rods and coryneformbacteria (polymorphic type), are known, and it is known that bacteriacausing odor of the armpit, which is particularly a problem, arecoryneform bacteria. The main components of the decomposition productsdue to such indigenous dermal bacteria are fatty acids having a carbonnumber of not more than 10, such as acetic acid, propionic acid,isobutyric acid, isovaleric acid, caproic acid and capric acid.

As conventional methods for removing or deodorizing such a body odor,suppressing the body odor by a bactericide or an antisweat agent ormasking the body odor by an aromatic is performed. However, with respectto the conventional bactericides, the minimum use thereof is desiredfrom a problem of safety in the human body, and also with respect toantisweat agents, the use thereof is limited only to application tospecific local areas because it suppresses important physiologicalfunction of the human body. Therefore, for example, at a portion such asthe armpit, where sweat and sebum are secreted and indigenous dermalbacteria are likely to grow, it is difficult to sufficiently preventbody odor. Further, masking body odor by an aromatic is likely to causemalodor by mixing of the smell of the aromatic and the body odor.

In order to solve such problems, some antibacterial agents safe to thehuman body are proposed. For example, in JP-A-SHO 61-291503, anantibacterial/anticultural agent, whose active ingredient is a mixtureof the sap of yucca and an acid such as acetic acid or propionic acid,is proposed. However, because acetic acid or propionic acid itself is acomponent evolving malodor of the body odor, such an agent is not alwayspractical.

In JP-A-SHO 60-42765 and JP-A-HEI 2-40043, an antibacterial agent, whichcontains natural farnesol and a synthetic farnesol as its activeingredients, is disclosed. Although these active ingredients areefficacious against bacteria of the genus Staphylococcus, they are weakin antibacterial properties against bacteria of the genusCorynebacterium, and data of antibacterial property to other indigenousdermal bacteria such as bacteria of the genus Propionibacterium are notdisclosed.

Further, in JP-A-HEI 8-40861, a method for preventing and treating thefoot odor using a monoglycerine ester of a middle chain fatty acid isproposed. Even in this method, because a component evolving malodor suchas caprylic acid or capric acid is generated from the monoglycerineester of the middle chain fatty acid by lipase action caused byindigenous dermal bacteria, it is not always practical.

Pimples are a dermal disease expressed mainly in puberty and the diseaseis called acne, and clinically they are defined as "chronic inflammatoryvariation generating in pores around the hair follicle fatty gland".Although pimples are a dermal disease caused by complicatedly entangledfactors, generally it is considered that excessive secretion of sebum,cornification of hair follicles and bacteria in hair follicles have animportant function therefor.

It is known that bacteria causing pimples are Propionibacterium acneswhich are coryneform bacteria. The bacteria grow in trichocyte, producelipase and hydrolyze triglyceride which is a major component in sebum,thereby producing free fatty acid and causing local inflammation. Thisis considered to be a main reason for generation of pimples.

As conventional methods for preventing or treating such pimples,suppression of secretion of sebum by female sex hormones, sterilizationby antibiotics etc. and breakaway of keratin by sulfur etc. areconducted. However, there is a fear of side effects in use of female sexhormones, in use of antibiotics there is a fear which also breaks amicrobial flora on derma useful to the human body, and in use of sulfurthere is a problem in stimulation of derma and generation of sulfursmell.

From such circumstances, development of safe antibacterial agents whichcan suppress the growth of indigenous dermal bacteria and suppress theevolution of body odor even in a portion where sweat or sebum is muchsecreted in the human body, and development of safe antibacterial agentswhich are efficacious in suppressing the body odor and preventing andtreating pimples without breaking microbial flora of indigenous dermalbacteria by preferentially suppressing coryneform bacteria which causethe armpit odor or pimples, are required.

DISCLOSURE OF THE INVENTION

As the result of earnest investigation to satisfy the above-describedrequirements, the inventors of the present invention have found thatspecified macrocyclic lactones and macrocyclic ketones, which aresynthetic aromatics of a musky odor, among aromatic compounds indicatestrong antibacterial properties against indigenous dermal bacteria.

An object of the present invention is to provide antibacterial agentswhich can be applied to various uses for suppressing the growth ofindigenous dermal bacteria, specifically, safe antibacterial agentsefficacious in suppressing body odor and preventing pimples,particularly, useful for application in cosmetics and in clothing.

Another object of the present invention is to provide fragrant cosmeticscontaining the forgoing antibacterial agents, and useful in clothing forimpregnating the antibacterial agents.

The, the macrocyclic lactones themselves are known aromatic compounds.Although it is described in Japanese cosmetics technology conferencereport (Sawano et al., 1993, Vol. 27 (3), page 227) that a form ofmacrocyclic lactone, for example, 15-pentadecanolide (orcyclopentadecanolide) indicates an antibacterial property againstbacteria of the genus Arthrobacter, it does not disclose at all thatsuch a macrocyclic lactone has an antibacterial action against bacteriaof the genus Staphylococcus, the genus Corynebacterium, etc. which areindigenous dermal bacteria.

To accomplish the above-described objects, an antibacterial agentaccording to the present invention contains at least one of amacrocyclic lactone represented by the following chemical formula (1)(In the formula, "n" is an integer in the range of 0-2, the portionsshown by "---" are single bonds or any one portions shown by "---" is adouble bond and/or and a macrocyclic ketone represented by the followingchemical formula (2), in which, "n" is an integer in the range of 0-2, Ris a hydrogen atom or a methyl group, the portions shown by "---" aresingle bonds or any one portion of the portions shown by "---" is adouble bond. ##STR1##

In the above described chemical formulae (1) and (2), in a case wherethe portions shown by "---" are single bonds, it is indicated that themacrocyclic lactone or the macrocyclic ketone is a saturated compound,and in a case where any one portions shown by "---" is a double bond, itis indicated that the macrocyclic lactone or the macrocyclic ketone isan unsaturated compound. Where, that "any one portion of the portionsshown by "---" is a double bond" means that only any one portion among aplurality of portions shown by "---" is a double bond for example, inthe case of the chemical formula of the above-described macrocyclicketone, means that only and one portion among three portions indicatedby 5-, 8-and 9-positions is a double bond.

The above described macrocyclic lactone comprises, for example, at leastone lactone selected from the group consisting of 14-tetradecanolide,15-pentadecanolide, 11(or 12)-pentadecen-15-olide, 16-hexadecanolide and9-hexadecen-16-olide. Among these, particularly, 14-tetradecanolide,15-pentadecanolide and 11(or 12)-pentadecen-15-olide are preferred. Theabove-described macrocyclic ketone comprises, for example, at least oneketone selected from the group consisting of cyclopentadecanone,3-methyl-cyclopentadecanone, cyclohexadecanone, 5-cyclohexadecen-1-one,8-cyclohexadecen-1-one, cycloheptadecanone and 9-cycloheptadecen-1-one.

Such an antibacterial agent indicates an excellent property forsuppressing the growth of bacteria, specifically against coryneformbacteria which are Gram-positive rods, in particular, against bacteriaof the genus Corynebacterium which affect evolution or acceleration ofthe armpit odor or Propionibacterium acnes which affect generation ofpimples. Therefore, this antibacterial agent has an excellent propertyfor suppressing body odor or/and an excellent property for suppressingpimples, an excellent property for suppressing body odor or/and theexcellent property for suppressing pimples can be obtained byadministering it in cosmetics used for suppressing body odor pimples,and an excellent antibacterial/deodorizing effect can be obtained byimpregnating it into fibers or clothing, particularly into clothingcoming into contact directly with the skin such as underwear, shirts,undergarments and socks.

THE BEST MODE FOR CARRYING OUT THE INVENTION

The antibacterial agent according to the present invention contains atleast one of a macrocyclic lactone represented by the aforementionedchemical formula (1) and/or a macrocyclic ketone represented by theaforementioned chemical formula (2). First, the antibacterial agentcontaining the macrocyclic lactone (1) will be explained.

Although it has been reported that a kind of lactone among knownaromatic compounds indicates an antibacterial property against specifiedbacteria, the antibacterial property of a macrocyclic lactone is notreported so much.

Surprisingly, a specified macrocyclic lactone represented by theaforementioned chemical formula (1) according to the present inventionindicates a strong antibacterial property against Gram-positive bacteriaof the genus Micrococcus, the genus Staphylococcus, the genusCorynebacterium, the genus Propionibacterium, etc., and can suppressbody odor by suppressing the growth of these bacteria. Further, becausepimples, which generate mainly in fat-leaking portions on the head, theface, the breast and the backs of males and females in puberty andyounger days in which secretion of fatty glands is active, are causedmainly by the growth of Propionibacterium acnes, the macrocyclic lactoneaccording to the present invention effective for suppressing this growthis also efficacious in preventing pimples.

The macrocyclic lactone according to the present invention can beprepared according to a regular method by synthesizing ω-oxyfatty acidand by intramolecular ring closing.

The macrocyclic lactone used in the present invention is good inbiodegradation and toxicity is not recognized, and therefore, it doesnot affect the ecosystem even if it is discharged in the environment. Itis safe to the human body.

Accordingly, because the antibacterial agent according to the presentinvention indicates a property for suppressing growth particularlyagainst indigenous dermal bacteria, it is preferably used by applicationto cosmetics and clothes objectifying the human body. As to cosmetics,hair care products such as shampoo, rinse, hair tonic and hair promoter,body cleanners such as soap and body shampoo, antisweat or deodorantproducts for armpit or foot, etc. can be raised, and the antibacterialagent according to the present invention can be used by addition tothese cosmetics. Although the amount of addition thereof may varydepending upon the kind or the purpose for use of the cosmetics, theamount is preferably in the range of 0.001-10 wt. % relative to thetotal weight, more preferably in the range of 0.01-5 wt. %. Further, itis possible to obtain an antibacterial/deodorizing effect byimpregnating the antibacterial agent according to the present inventioninto clothes such as underwear and socks. The impregnation of theantibacterial agent into clothes can be performed by a method such ascoating, dipping or spraying, and preferably, it can be impregnated atthe time of cleaning or washing of clothes by adding it to a detergent.In a case where the cloth is composed of synthetic fibers, theantibacterial agent may be mixed at the time of melt-spinning.

Next, the antibacterial agent containing the macrocyclic ketonerepresented by the chemical formula (2) will be explained.

The macrocyclic ketone represented by the aforementioned chemicalformula (2) according to the present invention has a particular propertyfor suppressing the growth of indigenous dermal coryneform bacteria, andhas an effect to suppress body odor and to prevent and treat pimpleswithout breaking the microbial flora of indigenous dermal bacteria.

The macrocyclic ketone according to the present invention can beprepared according to a regular method by ring expansion usingcyclododecanone as the raw material, and it may be an optically activesubstance.

The macrocyclic ketone used in the present invention is also good inbiodegradation and toxicity is not recognized, and therefore, it doesnot affect the ecosystem even if it is discharged in the environment. Itis safe to the human body. Accordingly, the antibacterial agentaccording to the present invention containing this macrocyclic ketone ispreferably applied to various cosmetics and clothes similarly to theabove-described antibacterial agent containing the macrocyclic lactone.Although the amount of addition thereof may vary depending upon the kindor the purpose for use of the cosmetics, the amount is preferably in therange of 0.001-10 wt. % relative to the total weight, more preferably inthe range of 0.01-5 wt. %.

Further, it is possible to obtain an antibacterial/deodorizing effect byimpregnating the antibacterial agent containing this macrocyclic ketoneinto clothes such as underwear and socks. The impregnation of theantibacterial agent into clothes can be performed by a method such ascoating, dipping or spraying, as aforementioned. Further, in a casewhere the cloth is composed of synthetic fibers, the antibacterial agentmay be mixed at the time of melt-spinning.

It is possible that the above-described macrocyclic lactone andmacrocyclic ketone are together contained in the antibacterial agent.Even in this case, the amount of addition of the antibacterial agent ispreferably in the range of 0.001-10 wt. %, and more preferably in therange of 0.01-5 wt. %, relative to the total weight of the cosmetic.

In the antibacterial agents and the cosmetics and clothes using theantibacterial agents according to the present invention, as long as theadvantages according to the present invention are not damaged,supplementary components, such as another antibacterial agent,astringent, bactericide, dermal secretion retarder, keratin breakawayagent, surfactant, thickener, aromatic, pigment, alcohol and water, maybe together used.

According to the above-described antibacterial agents of the presentinvention, antibacterial agents suitable to various uses for suppressingthe growth of indigenous dermal bacteria, particularly, suitable to safecosmetics and fibers and clothes efficacious in suppressing the bodyodor and in preventing and treating pimples, can be obtained.

Further, the macrocyclic lactone and macrocyclic ketone according to thepresent invention indicate a particular, selective property forsuppressing, in particular, the growth of indigenous dermal coryneformbacteria, and have an effect to suppress body odor and to prevent andtreat pimples without breaking the microbial flora of indigenous dermalbacteria. Because these macrocyclic lactones and macrocyclic ketones aregood in biodegradation and toxicity is not recognized, they do notaffect the ecosystem even if they are discharged in the environment aswaste, and they are safe to the human body.

Moreover, because the cosmetics containing the above-describedantibacterial agents are fragrant, for example, if the antibacterialagents are added to cosmetics containing sulfur for preventing ortreating pimples, not only the antibacterial effect but also a maskingeffect of sulfur smell by the musk-like fragrance can be obtained.Further, in the clothes impregnated with the antibacterial agents, bodyodor can be suppressed in an environment soft to the skin as well as thefragrance can be given.

Next, the present invention will be explained based on examinations andexamples.

First, the antibacterial agents and the cosmetics containing themacrocyclic lactone according to the present invention will beexplained.

(Examination)

Using the following liquids prepared for the test, 7 kinds of strainsand 2 kinds of culture media, the examination of antibacterial propertywith respect to the macrocyclic lactone was performed.

Prepared Test Liquids:

The solution mixing each of the following test compounds (macrocycliclactones) and polyoxyethylene cured castor oil (40 E.O. [additional molnumber of ethylene oxide: 40]) at equal contents was used after dilutingit ten times with distilled water. As a comparison,isopropylmethylphenol, which was a bactericide, was used as the testliquid.

Macrocyclic Lactones:

No. 1: 12-dodecanolide (saturated compound)

No. 2: 13-tridecanolide (saturated compound)

No. 3: 14-tetradecanolide (saturated compound)

No. 4: 15-pentadecanolide (saturated compound)

No. 5: 11(or 12)-pentadecen-15-olide (unsaturated compound)

No. 6: 16-hexadecanolide (saturated compound)

No. 7: 9-hexadecen-16-olide (unsaturated compound)

Comparison (bactericide):

No. 8: isopropylmethylphenol

Used Strains:

Gram-positive-aerobic bacteria

Micrococcus sp. (referred to as "M.sp")

Staphylococcus epidermidis (referred to as "S.e")

Staphylococcus aureus (referred to as "S.a")

Corynebacterium sp. (referred to as "C.sp")

Gram-positive-anaerobic bacteria

Propionibacterium acnes (referred to as "P.a")

Gram-negative-aerobic bacteria

Pseudomonas aeruginosa (referred to as "Ps.a")

Gram-negative-anaerobic bacteria

Escherichia coli (referred to as "E.c")

Used Culture Media:

For aerobic bacteria: normal bouillon medium (produced by Eiken ChemicalCorporation)

For anaerobic bacteria: GAM bouillon "Nissui" (produced by NissuiSeiyaku Corporation)

Each culture medium of 100 ml was put in an Erlenmeyer flask having acapacity of 500 ml, a suspension of each of the bacteria was inoculatedto achieve 10⁶ CFU/ml (colony forming units/ml), the test liquid wasadded into it so that the concentration of the test compound became 0(blank), 10 and 100 ppm, respectively, as shown in Table 1, and after asilicone gas-permeable plug was attached, at 37° C. for 24 hours, 80 rpmreciprocally shaking culture was conducted as to the aerobe and staticculture was conducted as to the anaerobe, respectively. Thereafter, theturbidity of the culture liquid (absorbance at a wave length of 660 nm)was determined.

As a result, as shown in Table 1, the macrocyclic lactones did notindicate a growth suppressing property against Gram-negative bacteriabut indicated a growth suppressing property against Gram-positivebacteria, and in particular, strong growth suppressing properties couldbe recognized in 14-tetradecanolide having a carbon number of 14 and15-pentradecanolide and 11(or 12)-pentadecen-15-olide having a carbonnumber of 15.

                  TABLE 1                                                         ______________________________________                                        Macro-  Concen-                                                                 cyclic tration Used Strain                                                  lactone No.                                                                           ppm     M.sp    S.e S.a  C.sp P.a  Ps.a E.c                           ______________________________________                                        1       0       +       +   +    +    +    +    +                                10 + + + + + + +                                                              100 - - - - - + +                                                            2 0 + + + + + + +                                                              10 + + + + + + +                                                              100 - - - - - + +                                                            3 0 + + + + + + +                                                              10 - - - - - + +                                                              100 - - - - - + +                                                            4 0 + + + + + + +                                                              10 - + - - + + +                                                              100 - - - - - + +                                                            5 0 + + + + + + +                                                              10 - + - - - + +                                                              100 - - - - - + +                                                            6 0 + + + + + + +                                                              10 + + + - + + +                                                              100 - - - - - + +                                                            7 0 + + + + + + +                                                              10 + + + + + + +                                                              100 - - - - - + +                                                            8 0 + + + + + + +                                                             (Compar- 10 + + + + + + +                                                     ison) 100 - - - - - + +                                                     ______________________________________                                         -: growth; none                                                               +: growth; present                                                       

EXAMPLES Examples 1, 2 and Comparative Example 1 (hair tonic)

Each of 10 males used the hair tonics of Example 1 and ComparativeExample 1 shown in Table 2 and the hair tonic of EXAMPLE 2 shown inTable 3 after washing of the hair by a shampoo, and the effect forsuppressing the smell of the head skin after 10 hours was estimated. Asa result, as shown in table 4, in the hair tonics of Examples 1 and 2,an effect for suppressing the smell of the head skin could be clearlyrecognized as compared with the hair tonic of Comparative Example 1.

                  TABLE 2                                                         ______________________________________                                                                  Comparative                                            Example 1 Example 1                                                          Component (wt. %) (wt. %)                                                   ______________________________________                                        14-tetradecanolide                                                                             0.3      --                                                    ethanol 60.0  60.0                                                            polyoxyethylene 1.0 1.0                                                       oleylalcohol(20 E.O.)                                                         aromatic 0.2 0.2                                                              distilled water remaining remaining                                            amount amount                                                              ______________________________________                                    

                  TABLE 3                                                         ______________________________________                                                         Example 2                                                      Example (wt. %)                                                             ______________________________________                                        15-pentadecanolide                                                                             0.3                                                            ethanol 60.0                                                                  polyoxyethylene 1.0                                                           oleylalcohol(20 E.O.)                                                         aromatic 0.2                                                                  distilled water remaining                                                      amount                                                                     ______________________________________                                    

                  TABLE 4                                                         ______________________________________                                                                          Comparative                                    Example 1 Example 2 Example 1                                                 (Number of (Number of (Number of                                             Estimation persons) persons) persons)                                       ______________________________________                                        Very efficacious                                                                          7           8         0                                             Efficacious 2 1 2                                                             A little 1 1 2                                                                efficacious                                                                   Not efficacious 0 0 6                                                         Deteriorated 0 0 0                                                          ______________________________________                                    

Examples 3-5 and Comparative Example 2 (deodorant lotion)

Each of 10 males having the armpit odor applied the deodorant lotions ofExamples 3 and 4 and Comparative Example 2 shown in Table 5 and thedeodorant lotion of Example 5 shown in Table 6 on the armpit aftertaking a bath, and the effect for suppressing the armpit odor after 10hours was estimated. As a result, as shown in Table 7, in the deodorantlotions of Examples 3-5, an effect for suppressing the armpit odor couldbe clearly recognized as compared with the deodorant lotion ofComparative Example 2.

                  TABLE 5                                                         ______________________________________                                                                          Comparative                                    Example 3 Example 4 Example 2                                                Component (wt. %) (wt. %) (wt. %)                                           ______________________________________                                        15-pentadecanolide                                                                          0.1        1.0      --                                            chlorohydroxyl 10.0  10.0  10.0                                               aluminium                                                                     ethanol 70.0  70.0  70.0                                                      polyoxyethylene 1.5 1.5 1.5                                                   oleylalcohol(20 E.O.)                                                         aromatic 0.1 0.1 0.1                                                          distilled water remaining remaining remaining                                  amount amount amount                                                       ______________________________________                                    

                  TABLE 6                                                         ______________________________________                                                         Example 5                                                      Component (wt. %)                                                           ______________________________________                                        11 (or 12)-pentadecen-                                                                         1.0                                                            15-olide                                                                      chlorohydroxyl 10.0                                                           aluminium                                                                     ethanol 70.0                                                                  polyoxyethylene 1.5                                                           oleylalcohol(20 E.O.)                                                         aromatic 0.1                                                                  distilled water remaining                                                      amount                                                                     ______________________________________                                    

                  TABLE 7                                                         ______________________________________                                                                             Comparative                                 Example 3 Example 4 Example 5 Example 2                                       (Number of (Number of (Number of (Number of                                  Estimation persons) persons) persons) persons)                              ______________________________________                                        Very    9         10         10      0                                          effica-                                                                       cious                                                                         Effica- 1 0 0 3                                                               cious                                                                         A little 0 0 0 6                                                              effica-                                                                       cious                                                                         Not 0 0 0 1                                                                   effica-                                                                       cious                                                                         Deterio- 0 0 0 0                                                              rated                                                                       ______________________________________                                    

Next, the antibacterial agents and the cosmetics containing themacrocyclic ketone according to the present invention will be explained.

(Examination)

Using the following 7 kinds of liquids prepared for the test, 7 kinds ofstrains and 2 kinds of culture media, the examination of antibacterialproperty was performed. Prepared test liquids:

The solution mixing each of the following No. 1-7 macrocyclic ketonesand polyoxyethylene cured castor oil (40 E.O.) at equal contents wasused after diluting it ten times with distilled water.

Macrocyclic Ketones:

No. 1: cyclopentadecanone (saturated compound)

No. 2: 3-methyl-cyclopentadecanone (saturated compound)

No. 3: cyclohexadecanone (saturated compound)

No. 4: 5-cyclohexadecen-1-one (unsaturated compound)

No. 5: 8-cyclohexadecen-1-one (unsaturated compound)

No. 6: cycloheptadecanone (saturated compound)

No. 7: 9-cycloheptadecen-1-one (unsaturated compound)

Used Strains:

Gram-positive rods (coryneform bacteria)

Corynebacterium sp. (referred to as "C.sp")

Propionibacterium acnes (referred to as "P.a")

Brevibacterium epidermidis (referred to as "B.e")

Gram-positive coccus

Staphylococcus epidermidis (referred to as "S.e")

Staphylococcus aureus (referred to as "S.a")

Gram-negative rods

Pseudomonas aeruginosa (referred to as "Ps.a")

Escherichia coli (referred to as "E.c")

Used Culture Media:

For aerobic bacteria: normal bouillon medium (produced by Eiken ChemicalCorporation)

For anaerobic bacteria: GAM bouillon "Nissui" (produced by NissuiSeiyaku Corporation)

Each culture medium of 100 ml was put in an Erlenmeyer flask having acapacity of 500 ml, suspension of each bacteria was inoculated toachieve 10⁵ CFU/ml, the test liquid was added into it so that theconcentration of each macrocyclic ketone became 0 (blank), 10 and 100ppm, respectively, and after a silicone gas-permeable plug was attached,at 37° C. for 10 hours, 80 rpm reciprocally shaking culture wasconducted as to the aerobe and static culture was conducted as to theanaerobe, respectively. Thereafter, the turbidity of the culture liquid(absorbance at a wave length of 660 nm) was determined. In thisexamination, only propionibacterium acnes, which was strict anaerobe,was cultivated anaerobically.

As a result, as shown in Table 8, the macrocyclic ketones did not at allindicate a growth suppressing property against Gram-negative bacteriabut indicate a growth suppressing property against Gram-positivebacteria. Among these, they indicated a particular growth suppressingproperty against coryneform bacteria, and particularly, in themacrocyclic ketones whose "n" is 1 or 2 in the aforementioned chemicalformula (2), strong growth suppressing properties could be recognizedagainst any strains of coryneform bacteria.

                  TABLE 8                                                         ______________________________________                                                 Used strain                                                          Macro-         Gram-positive      Gram-                                       cyclic Concen- Rod (coryneform      negative                                    ketone tration bacteria) Coccus Rod                                         No.    ppm     C.sp    P.a B.e   S.a S.e  Ps.a E.c                            ______________________________________                                        1      0       +       +   +     +   +    +    +                                 10 - - + + + + +                                                              100 - - + + + + +                                                            2 0 + + + + + + +                                                              10 - - + + + + +                                                              100 - - + + + + +                                                            3 0 + + + + + + +                                                              10 - - - + + + +                                                              100 - - - - + + +                                                            4 0 + + + + + + +                                                              10 - - - + + + +                                                              100 - - - - + + +                                                            5 0 + + + + + + +                                                              10 - - - + + + +                                                              100 - - - - + + +                                                            6 0 + + + + + + +                                                              10 - - - + + + +                                                              100 - - - - - + +                                                            7 0 + + + + + + +                                                              10 - - - + + + +                                                              100 - - - - - + +                                                          ______________________________________                                         - : growth; none                                                              + : growth; present                                                      

EXAMPLES Examples 6 and Comparative Example 3 (deodorant lotion)

Each of 10 males having the armpit odor applied the deodorant lotions ofExample 6 and Comparative Example 3 shown in Table 9 on the armpit aftertaking a bath, and the effect for suppressing the armpit odor after 10hours was estimated. As a result, as shown in Table 10, in the deodorantlotion of Example 6, an effect for suppressing the armpit odor could beclearly recognized as compared with the deodorant lotion of ComparativeExample 3. This Comparative Example 3 is the same as the aforementionedComparative Example 2.

                  TABLE 9                                                         ______________________________________                                                                  Comparative                                            Example 6 Example 3                                                          Component (wt. %) (wt. %)                                                   ______________________________________                                        5-cyclohexadecen-1-one                                                                         0.1      --                                                    chlorohydroxyl 10.0  10.0                                                     aluminium                                                                     ethanol 70.0  70.0                                                            polyoxyethylene 1.5 1.5                                                       oleylalcohol(20 E.O.)                                                         aromatic 0.1 0.1                                                              distilled water remaining remaining                                            amount amount                                                              ______________________________________                                    

                  TABLE 10                                                        ______________________________________                                                                 Comparative                                             Example 6 Example 3                                                           (Number of (Number of                                                        Estimation persons) persons)                                                ______________________________________                                        Very efficacious                                                                             9         0                                                      Efficacious 1 3                                                               A little 0 6                                                                  efficacious                                                                   Not efficacious 0 1                                                           Deteriorated 0 0                                                            ______________________________________                                    

Example 7 and Comparative Example 4 (cream for pimples)

Each of 10 males in twenties having pimples applied the cream of Example7 shown in Table 11 onto the right half of the face and the cream ofComparative Example 4 onto the left half of the face after taking abath, every day for one month. As a result, as shown in Table 12, inExample 7, an effect for treating pimples could be clearly recognized ascompared with Comparative Example 4. Moreover, masking effect of sulfursmell was also recognized.

                  TABLE 11                                                        ______________________________________                                                                   Comparative                                           Example 7 Example 4                                                          Component (wt. %) (wt. %)                                                   ______________________________________                                        9-cycloheptadecen-1-one                                                                         0.3      --                                                   sulfur 3.0 3.0                                                                glycerinemonostearate 3.0 3.0                                                 polyoxyethylene 1.0 1.0                                                       oleylalcohol(20 E.O.)                                                         beeswax 3.0 3.0                                                               liquid paraffin 10.0  10.0                                                    vaseline 5.0 5.0                                                              squalene 30.0  30.0                                                           propylene glycol 5.0 5.0                                                      paraoxybutyl benzoate 0.1 0.1                                                 aromatic  0.05  0.05                                                          distilled water remaining remaining                                            amount amount                                                              ______________________________________                                    

                  TABLE 12                                                        ______________________________________                                                                 Comparative                                             Example 7 Example 4                                                           (Number of (Number of                                                        Estimation persons) persons)                                                ______________________________________                                        Very efficacious                                                                             7         0                                                      Efficacious 2 1                                                               A little 1 2                                                                  efficacious                                                                   Not efficacious 0 7                                                           Deteriorated 0 0                                                            ______________________________________                                    

Example 8 and Comparative Example 5 (antibacterial agent for clothes)

After taking a bath, each of 10 males put on the socks each sprayed withthe antibacterial agent for clothes of Example 8 and the antibacterialagent for clothes of Comparative Example 5 shown in Table 13 for tenhours, and the intensity of the foot odor of the socks after wearing wasestimated. As a result, as shown in Table 14, in Example 8, an effectfor suppressing the foot odor could be clearly recognized as comparedwith Comparative Example 5.

                  TABLE 13                                                        ______________________________________                                                                  Comparative                                            Example 8 Example 5                                                          Component (wt. %) (wt. %)                                                   ______________________________________                                        15-pentadecanolide                                                                             1.0      --                                                    polyoxyethylene 1.0 1.0                                                       oleylalcohol(20 E.O.)                                                         aromatic 0.1 0.1                                                              ethanol remaining remaining                                                    amount amount                                                              ______________________________________                                    

                  TABLE 14                                                        ______________________________________                                                                   Comparative                                           Example 8 Example 5                                                           (Number of (Number of                                                        Component persons) persons)                                                 ______________________________________                                        Foot odor is not present                                                                       2         0                                                    at all.                                                                       Almost not present 5 0                                                        slightly present 3 3                                                          Foot odor is strong. 0 5                                                      Very strong 0 2                                                             ______________________________________                                    

Industrial Applications of the Invention

The antibacterial agents containing the specified macrocyclic lactoneor/and macrocyclic ketone indicate an excellent property for suppressingthe growth against specified indigenous dermal bacteria, in particular,suppress the evolution of the body odor, and they are useful tocosmetics used for the purpose of preventing or treating pimples, and toclothes.

We claim:
 1. An antibacterial agent selected from the group consistingof at least one of a macrocyclic lactone and a macrocyclic ketone, saidmacrocyclic lactone being represented by the following chemical formula1, where "n" is an integer in the range of 0-2, the designations "---"are single bonds or any one portion of the portions shown by "---" is adouble bond, and said macrocyclic ketone being represented by thefollowing chemical formula (2), where "n" is an integer in the range of0-2, R is a hydrogen atom or a methyl group, and the designations "---"are single bonds or any one portion of the portions shown by "---" is adouble bond. ##STR2##
 2. The antibacterial agent according to claim 1,wherein said macrocyclic lactone and macrocyclic ketone have a potencyfor suppressing the growth of indigenous dermal bacteria.
 3. Theantibacterial agent according to claim 2, wherein said indigenous dermalbacteria are coryneform bacteria.
 4. The antibacterial agent accordingto claim 3, wherein said coryneform bacteria are at least one ofbacteria of the genus Corynebacterium and the genus Propionibacterium.5. The antibacterial agent according to claim 1, wherein saidmacrocyclic lactone is at least one selected from the group consistingof 14-tetradecanolide, 15-pentadecanolide, 11(or12)-pentadecen-15-olide, 16-hexadecanolide and 9-hexadecen-16-olide. 6.The antibacterial agent according to claim 1, wherein said macrocyclicketone is at least one selected from the group consisting ofcyclopentadecanone, 3-methyl-cyclopentadecanone, cyclohexadecanone,5-cyclohexadecen-1-one, 8-cyclohexadecen-1-one, cycloheptadecanone and9-cycloheptadecen-1-one.
 7. The antibacterial agent according to any oneof claims 1 to 6, wherein said antibacterial agent has a property forsuppressing the body odor or/and a property for suppressing pimples. 8.The antibacterial agent according to claim 7 combined with a cosmetic.9. A cosmetic containing the antibacterial agent according to claim 7.10. The cosmetic according to claim 9 having a property for suppressingbody odor or/and a property for suppressing pimples.
 11. A clothimpregnating the antibacterial agent according to claim
 7. 12. The clothaccording to claim 11 having at least an antibacterial/deodorizingeffect.